: Looking for ideas and any links you may have to serious kayak
: sailing info. Not downwind sails, but real sailing rigs that go
: upwind. I am thinking outriggers and some sort of centerboard or
: leeboard set up.

: . . .

I sailed an old fiberglass canoe several years ago; I knew little about sailing back. I built a single outrigger float for it with a pivoted leeboard and about 35 SF (3.25 m2) sail. The leeboard worked OK - about 6 to 10% of sail area immersed is about right, the mast broke off first time, I added standing rigging and the mast then broke in the middle; also I got the rigging tangled. First lesson was, there’s a surprising amount of power in the wind; second lesson - keep it simple . . .

Eventually I got it to work and it sailed rather slowly with a lot of noise from the float; I used to sail it with plenty of weight on the float, figuring that would be balanced. Then one day things got quiet and the boat suddenly picked up a lot of speed. I realized the float was out of the water: third lesson, sail with the floats out of the water and have one on each side . . .

Most kayaks and canoes are designed to track well so turning can be slow and tacking is often a problem; an extra large rudder is probably a good idea.

With decent floats a lot more sail area can be accommodated - I was too chicken. Even if a gust pushes a float underwater the drag slows the roll and gives you time to spill air or balance the boat with body weight. I am not sure about sailing without outriggers though, a decked sailing canoe is a lot more stable than a typical kayak and has more space to move around and balance the sail forces.

BTW: I experimented with a tiny (15 SF/1.5 M2) sail on a small kayak using a Bruce foil (plenty of info on these on the net) which worked really well, but never got around to making a bigger rig. Again the biggest problem was slow turning.